


Friends Don't

by anniesardors



Series: Like a Love Song [3]
Category: Chicago PD (TV)
Genre: F/M, Flirting, Jealousy, halstead brothers
Language: English
Status: Completed
Published: 2021-02-12
Updated: 2021-02-12
Packaged: 2021-03-12 02:46:56
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,809
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29378001
Author URL: https://archiveofourown.org/users/anniesardors/pseuds/anniesardors
Summary: After Hailey goes out with another guy, Jay finds himself drinking away his pain at Molly's. After a heart to heart with Will, Jay comes to the realization that he and Hailey do a lot of things that friends don't. (Fluffy Jealousy Fic for Day 5 of the Upstead Love Song Challenge)
Relationships: Jay Halstead & Hailey Upton, Jay Halstead/Hailey Upton
Series: Like a Love Song [3]
Series URL: https://archiveofourown.org/series/2151000
Comments: 2
Kudos: 64





	Friends Don't

**Author's Note:**

> Welcome back to another oneshot for the Upstead Valentine's Love Song Challenge on Tumblr! Today's prompt was the song "Friend's Don't" by Maddie and Tae
> 
> Hope you all enjoy! This was an incredibly fun one to write!

"You wanna go get drinks?"

It's Friday night, they just wrapped a big case and he's feeling good, so yeah, he asks his partner to go get drinks. It's part of their thing.

"Can't. I have plans."

Her answer catches him off guard. Maybe it had been bold of him to assume that she had nothing going on a Friday night, but most of her Friday nights were spent with him. And he had spent all week working beside her and she had not mentioned any type of plans.

"Oh, that's-"

His words are cut off by the vibrating of her phone on her desk. He is not trying to be nosy, but her phone is out in the open view and his stomach sinks when he sees the name on the phone.

**_Gabriel._ **

It would make him a bad partner if he did not know the names of the important people in her life (right, he reasons? Kevin must know the names of Adam's family and friends, right?)

But he does not recognize the name. He quickly scans his brain for the name. Her brothers are Daniel and Thomas. Her father is Nicholas. She does not have any CIs by that name and she has not mentioned any off the book work. For the life of him, he cannot think of another cop that she has worked with that is named Gabriel and he knows there is no one with that name at 51 or Med.

Being an elite detective, Jay quickly pieces together what is going on. Hailey is going out. On a date. With another guy.

"Sorry." She murmurs. "I'll see ya, Jay. Have a good night."

She turns to leave and he hears her soft laugh when she answers the phone and says "Hey Gabe."

It's going to be a long night.

* * *

He is four shots in by the time Will sits down next to him at Molly's, shaking his head. "I don't know what happened for you to be drinking like this."

"Nothing happened," Jay tells him through gritted teeth, waving Hermann over for another drink.

"Sure," Will says, not buying it. The doctor shrugs off his jacket and orders a beer before turning to his brother. "I have not seen you drink like this in a while. Normally it's one, maybe two drinks, so you are good to drive yourself and Hailey home."

 _Hailey_. The mention of her name is enough to make him let out a frustrated huff. The alcohol he has quickly downed throughout the night has allowed him to not focus (too much) on what his partner is doing. But now that he is in between shots and Will has brought her up, his mind is racing a mile a minute. He wonders how long she has been seeing this Gabe character? What does he do for a living? Does he treat her right?

If he was honest, Jay thought that he and Hailey had been getting closer during the past few months. The six weeks she was gone in New York, while incredibly hard, had allowed them to grow even closer in a new way. And ever since she got back, he thought they were moving towards actually becoming something.

But apparently, he was wrong. Dead wrong.

"So, Hailey's the reason we are drinking tonight?" Will asks and when his younger brother does not respond, he has his answer.

"She injured? Going back to New York?" Will says in between sips of his beer and Jay just shakes his head.

"She's fine. And she's staying in Chicago."

"So what is it?"

Jay sighs because actually having to say the words makes him feel stupid. He is a grown-ass man, an elite detective, and a war vet and he is really sitting here drinking away his sorrows because the girl he likes is out on a date with another guy.

"It's nothing, I'm good," Jay tells him, waving at Hermann for yet another drink, but Will shakes his head at the firefighter.

"Hey-"

"Just tell me what happened." His brother demands. "I won't laugh, I won't judge. I'll sit here quietly."

"You've never been quiet," Jay mutters and Will laughs.

"Well, then this is your one chance. Now spill."

His hands grip the edge of the bar and he lets out a long, low breath. "She's out with some guy."

"Okay?"

Jay shoots his brother a knowing look and Will registers what he means. "Got it. No offense bro, but maybe if you hadn't waited so long to ask her out-"

"I thought you weren't going to judge?" Jay cuts him off, shaking his head.

"Yeah, I lied." Will pushes his beer away from him, looking at his brother dead on. "Did she say if it was a date?"

"No-"

"So just tell her how you feel." The way his brother says it, it sounds like the simplest thing in the world. Like those three little words would not change his entire universe.

"I can't."

"Why?" Will pushes.

"Because we're friends."

"Bull," Will says and Jay makes a questioning face and begins to respond, but Will is quicker. "You two are a lot of things, but friends is not one of them."

"What are you talking about, Will?"

"You two are obviously in love with each other!" Will says in a hushed exclamation, mindful of the fact they are in a crowded bar.

"We are friends, Will. Good friends." He tries to convince his brother (himself?) Sure, he has feelings for Hailey, and maybe they are hitting him a little stronger tonight. But, clearly, he has misread the situation and she sees their dynamic as nothing more than a friendship.

"Alright," Will says with a sigh. "Who do you spend all your time with?"

"Hailey...but we are partners."

"But you spend all your off time together." Will points out. "And when she was gone, you were always on the phone with her. Even now that she is back, every time you come over to watch the game you are nonstop texting her."

Jay glares at him because while it's true, he spends an obscene amount of time with Hailey, his brother does not need to be proven right.

"I know for a fact that you get her coffee in the morning because every time we go for a run you have to leave early to get her one." Will continues. "I know that she steals your pens because she likes to tease you. And she checks your paperwork because your spelling has not improved since we were kids. You two eat dinner together almost every night and you have spare clothes at each other's places."

Taken aback by Will's rant, Jay opens his mouth to argue with his brother, but Will clearly isn't done. "And I knew all of that because you never shut up about her!"

With a frustrated groan, Jay drops his head to the bar counter. For being some who literally got paid to do undercover work, one would think Jay could hide his feelings for his partner a little bit better. Clearly not, though, because here he is, sitting in a bar, listening to his brother lecture him on the many reasons that he and Hailey are not just friends.

"So," Jay says, lifting his head and resting it in his hands. "I might have some feelings for her."

"Might? Some?"

"Okay!" His head snaps up quickly and his hands are frantic. "I like her, okay? A lot. You happy?"

"I'd be happier if you told her how you felt about her," Will tells him cheekily, earning him another Jay glare.

"Will-"

"Jay, it's not one-sided. Friends don't look at each other the way you two do, okay? Just trust me."

Jay doesn't respond and he is thankful when his brother slaps him on the back and tells him he is going to go say hi to some friends. If he thinks about it, his brother is right. Friends don't do the things that he and Hailey do. Hailey is the first person he texts when he wakes up and the last person he talks to before he goes to sleep. They know each other's coffee orders and they know what foods the other despises.

She keeps his favorite granola bars in her locker and he keeps a stash of her favorite candies in his. He has several of her sweatshirts in an empty drawer at his place and he definitely has a toothbrush and some other toiletries in her bathroom.

Hailey knows about his time in the war. She knows about the horrors he experienced in Chicago and she knows about his difficult relationship with her dad. He knows about her childhood, about the case where she lost Garrett, about how after she was meritoriously promoted, everyone made assumptions about her.

He knows far more than a friend should know about her. He knows everything.

Reaching into his pocket, he grabs his wallet and pulls a few bills out, slamming them on the counter, intent to leave this bar and figure out what the hell he was going to do about these feelings of his. But before he can leave, his phone buzzes.

**_You still at Molly's?_ **

It's from Hailey. Of course, it's from Hailey. Of course, she knows where he is.

She knows everything too.

He quickly texts back that he is and waits a few minutes for a response. The way his mood instantly changes at the idea of her coming to the bar is a clear indicator that maybe Will knows what he was talking about.

It is hard to miss as that familiar blonde hair and bright smile walk into the bar. Jay's stomach drops when he sees a man who he assumes is Gabriel walk in with her. He has a few inches on Hailey, but he is clearly shorter than Jay, with blonde hair and a broad frame.

"Jay!" Her voice is happy as makes her way over to him. "I want you to meet Gabe. Gabe, this is my partner, Jay."

Gabe sticks his hand out with a smile and Jay takes it, faking pleasantries for Hailey's sake. "Nice to meet you, man."

"You too. Hailey has told me a lot about you." Gabe responds and before Jay can shoot Hailey a smug look, she interrupts them.

"We were on our way back to my place and I wanted to stop in and say hi." She smiles at him shyly before turning to Gabe. "You wanna stay for a drink?"

Gabe shakes his head. "Nah, I really should get going."

The disappointment that grows on Hailey's face is not obvious to most, but he knows her, and he knows that she wishes Gabe gave a different answer.

Hailey nods and turns to Jay. "You drive here?"

"Yeah. But I can uber or get a ride with Will-"

"Nonsense." She takes the keys out of his hands and stuffs them in her own pocket. "You hate leaving your truck places. I'll drive you home. That way Gabe doesn't have to drop me off."

She looks up at Gabe as if to make sure that plan is good with him, and he nods. Part of him feels bad for ruining her night with Gabe, but another part of him is thankful that she is not going home with some other guy. As they leave the bar, Jay catches a smart look from Will that he chooses to ignore since Hailey is with him. The walk to the parking lot is quiet and Jay stands by awkwardly as Hailey hugs Gabe goodbye.

"Okay." Hailey finally says when they are settled in his truck. She is significantly shorter than him and it takes her a few minutes to adjust the seat so she could actually reach the petals. He knows it is going to be annoying to get everything put back to the way he likes it the next time he drives, but the sight of her driving his truck is more than worth it.

"You've clearly had several drinks. And you were sitting alone." She turns sideways in the driver's seat, lifting one leg onto the set and tucking it under her, the car still off. "Care to tell me what's going on?" 

"Hailey, it's a bar. People drink."

She raises her eyebrows, her telltale sign that she is not buying his story. He sighs, turning in his seat to let his body mirror hers. And maybe it's the alcohol or it's the talk with his brother or maybe it's just he is so damn tired of holding in these feelings that motivates him to say what he says next.

"I was drinking because you were out with Gabe." He says like a child who has been caught drawing on the walls by their parents. Her face softens, but she remains silent, so he takes a deep breath and continues. "I guess I was kinda jealous and I get that I don't get to be jealous because it's your life and you deserve to be happy even if that means dating Gabe because it's not your fault that I waited forever to actually ask you out and-"

The more he talks, the more he realizes he is quite drunk and he probably should have just gotten a ride home with Will.

Hailey, on the other hand, is sober and is laughing her ass off.

"I'm sorry, I'm sorry." She says after coming down from her laughing fit. He stares at her, confused and frankly, a little embarrassed because he just basically told her that he liked her, and here she is, laughing.

"I'm not laughing at you, it's just," Hailey chuckles again, shaking her head. "I'm not dating Gabe."

Scientifically, he knows it's impossible, but Jay swears he feels his body start to sober up as soon as the words are out of her mouth.

"Really?"

She nods. "He's my best friend from high school. We grab dinner a couple of times a year when our schedules line up." She pauses for a moment, before adding. "And he's married. Like super married with two kids."

Jay lets out a breath he didn't even know he was holding and before he can stop himself, he is laughing too, because of course, he drank himself sick out of jealousy only to have the guy be married. Not one of his proudest moments.

Hailey joins in his laughter and he feels himself calm down for a moment before he is once again struck with the realization that he drunkenly told Hailey he had feelings for her.

"Hailey-" He starts, but she cuts him off.

"You're an idiot, you know that. An absolute idiot." He knows that, of course, but he is confused as to which part of his stupidity she is referring to.

"I don't like Gabe, Jay. I like you. Heaven knows why."

His brain completely ignores the way she teases him, to focused on the three little words she just muttered here in the cold in his car. _I like you._

Hailey Upton liked him.

"Yeah?" He asks quietly and she lets out a breathy laugh.

"Yes. So next time I am on a date, how about you not drink like a fish and just talk to me instead, okay?"

"Well, hopefully, your next date will be with me, so that shouldn't be a problem."

He doesn't miss the way her lips form a sweet smile or the way her cheeks redden at his words. It's definitely not something a friend would notice, but he sees it right away.

"Good." She whispers. Her body is still curled up in the front seat of his truck and he leans himself against the center console, slowly, intent to show her properly what he feels for her, but before he can, he feels her hand pressing against his chest, pushing him back into his seat with a laugh.

"Oh no." She says between giggles. "We are not having our first kiss in the front seat of your truck while you are drunk."

He pouts, hoping she will maybe rethink her statement, but it just makes her laugh more. She grabs his keys from the cup holder and starts the engine. As she throws the truck in drive, she winks at him. "But definitely after you sober up."

"If I can't kiss you, can I at least tell you something?" She hums in agreement, eyes focused on the road, a smile still on her face.

"I think you look really hot driving my truck."

Her eyes widen and she glances at him, shocked at his boldness. "I don't think friends are supposed to say that."

"Yeah, well I don't think we are just friends."

She doesn't miss a beat when she replies, "Yeah, me either."

**Author's Note:**

> Reviews?
> 
> Follow me on tumblr anniesardors for more fics, to leave prompts, or to talk anything chicago pd and upstead!


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